Process for converting unsaturated oleic and fatty acids and their esters into saturated compounds.



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CARL HER-KEANE? EAUSAEEANN, QF HAMBURG, GERMANY, ASSIGNOR TO THE FIRMOF- IJE NORDIS'KE FABRIKER DE-NO-FA AKTIESELSKAP, 0F CHRISTIANIA,NORWAY.

PRQCE SSFOR CGNVEIR-TING UNSATURATED {PLEIC AND FATTY ACIDS AND THEIRESTERS INTO SATUBATIED COMPOUNDS.

' To all whom it may concern:

Be it known that I CARL HERMANN Hans- AMANN, a citizen of Switzerland,and resident of Hamburg, in the German Empire; have invented a certainnew and. useful Process for Converting Unsaturated Oleic and Fatty Acidsand Their Esters into Saturated Compounds, of which the following is aspecification.

It has been previously proposed to convert unsaturated fatty compounds,such as liquid oils or soft fats and unsaturated fatty acids or theiresters into saturated compounds, as solid fats or saturated fatty acidsor their esters, such processes being carried out by "means of hydrogenin the presence of finely divided metals 01' metallic compounds actingas,catalytic substances. For this purpose various metals in metalliccondition have been proposed, as Well as inorganic and organic salts orcompounds of such metals, from which the metal separates during thehardening operation and acts as a catalyiic metal, for exampleoxids,hydroxids, nitrates, formates and lactates; iin

soluble soaps of the heayy or noble metals have also been proposed. Allsuch catalysts heretofore used are insoluble in the fats or oils undertreatment, and the intimate mixture possible with a soluble substancecannot be obtained.

According to my invention the hydrogen conveying agentadded to theunsaturated substances consists of a basic compound of a suitable metal(for example, copper, nickel, cobalt, and other non-noble metals knownas catalytic agents, for hydrogenating fats or oils) with a fatty acidsoluble in the fatty compound to be treated, such for example as oleic,stearic, or like acid. Such basic metallic compounds may be formed fromthe substances to be treated, or from compounds similar thereto anddissolve in the melted fats or oils, and, on passing hydrogen throughthe mixture (at a temperature of say between 100 and 180 C.) a colloidalmetallic hydrid is formed that is regarded as the active agent in thereducing or hydrogenating action, which proceeds steadily. The hydridexists inthe mixture as long as there is free hydrogen 1 Specificationof Letters Patent.

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Patented July 6, 19 15.

Application filed flctober 'l, 1913. Serial No. 793,888.

present, and small additions onlyof such a fatty compound are suflicientto reducelarge quantities ofithe unsaturated materials. The same fattyacids as exist (usually as glycerids) in the compounds to be treated arepreferably employed to form the basic metallic compound used forcatalysis.

The change of the said basic metallic compounds into an activecondition, when dissolved in the fatty-material, takes place graduallyin the hydrogen atmosphere at temperatures above 100 CL but a highertemperature of, say, about 160 C. would be employed in practice. At thistempera ture the copper or other hydrid is obtained in colloidalcondition.-

As arr-example of the process the following may be taken :--500 parts byweight of raw soy-bean oil is mixed with 0.4 per cent. of thebasicoleate'of nickel (Ni (0H) a 35 2) 1 011 e idh) dissolved in the fat anduniformly distributcd throughout the whole mass. thecompound is actedupon by hydrogen with the formation of water and the mass becomes Atthis stage the freed hydroxyl group probably plays a part in theformation of a copperhydrid. By alternate formation and decomposition ofthis colloidal copper hydrid the hydrogen is ren- .dered active,converting the unsaturated fatty compounds into saturated, for instancethe oleic acid into stearic acid. Analogous rcactions occur with thevarious metallic compounds which may be employed in accordance with thisinvention. In no case is the metal itself produced or its oxid, as insome of the prior pmcesses, except he end of the'reaction, when freehydrogen is eliminated to, gradually decompose the'hydrid.

The reactions which occur may be given approximately by the followingequations,

taking copper as the metal and oleic acid as a typical fatty acid ofhigh molecular weight Formation of the primary catalyst Cu H Theresulting final reaction on, (CH2) 7 on, on, (CH2) 7 coon c n, 211,0 H

The fatty compound is now a saturated one.

' ine basicity necessary for the metallic salt 18 not necessarilyrepresented -by the formula given above, as, for example, either one ortwo molecules of copper hydroxid may react with a molecule of the fattyacid, and even more highly basic compounds are possible without theexistence of free hydroxid. polybasic salts are serviceable for the present purpose.

The new process offers many advantages over the hitherto knownprocesses. The product of the reaction is not polluted by foreignsubstai'ices, for example porous bodies, inorganic acids or volatileorganic acids, may be the case, for instance, if nickel format-e orlactate is used. The catalytically acting compounds of the non-nobleieavy metals (cop 'uer, nickel; iron, etc.) produce only fatty acids ofhigh molecular weight as by-products, which. acids may be those actuallycomposing the material under treatment so that, when the reaction iscompleted the resulting material contains no foreign acid or esters.

The forn'iation the metallic hydrid in the materialunder treatment acharacteristic of this process which from prior methods of hydrogenationemploying metallic organic compounds, where they metal itselfis producedin a finely divided condition.

The elimination of the metallic coni- Mixtures of normal anddistinguishes pounds from the hydrogenated fats or oils may be effectedby simply washing the lat ter with dilute acid, for example,hydrochloricacid.

To carry out the process simple apparatus of' known construction may beemployed.

In the present process the hydrogenation occurs at temperatures between100 and 180 (3., while if metallic oxids or metallic salts of the lowerfatty acids are used, higher temperatures are required.

I claim- 1. The process of convertingunsaturated fatty acids and theiresters into saturated compounds, which comprises acting upon anunsaturated fatty compound in the presence of hydrogen with a basicmetallic sah of the fatty compound treated.

2. The process of converting unsaturated fatty acids and their estersinto saturated compounds, which comprises acting upon an unsaturatedfatty compound at'a temperature above 100 C. in the presence of hydrogenwith a basic heavy metallic salt of the fatty compound treated.

The process of converting unsaturated fatty acids and their esters intosaturated compounds, which comprises acting upon an unsaturated fattycompound in the presence of hydrogen with a basic metallic salt of thefatty. con'ipound treated. and after the completion of the conversionconverting the hydrid to. metal in a form insoluble and stable'in theresultant product, and separating the metal.

4. A process for converting unsaturated fatty acids and their estersinto saturated compounds, which comprises acting upon an unsaturatedfatty compound in the pres ence hydrogen with a basic metallic salt of acompound similar to that treated.

5. The process of converting unsaturated fatty acids and their estersinto saturated compounds, which comprises acting upon an unsaturatedfatty compound in the presence of hydrogen with a'mixture of a basic andnormal metallic salt of the fatty compound treat-ed.

(5. The process of hardening oils, which comprises treating the'oil witha mixture of lam: and normal salts of a compound similar to that treatedand soluble therein.

,CARL HERMANN HAUSAMANN.

\Vitnesses F.. A. MAX KAEM err, Eounm) Horr.

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